Manchester United’s worst European draws in recent history

Many believe Manchester United often get it easy when it comes to Champions League knock-out draws, but today’s ceremony in Nyon should test them against the very best Europe has to offer in the quarter-finals.

United will be drawn against one of Barcelona, Real Madrid, Atletico Madrid, Chelsea, Borussia Dortmund, Paris Saint-Germain or champions Bayern Munich. Few fancy their chances, and it’s easy to see why.

Here are some other notable occasions when United have been drawn against fierce competition in the Champion’s League.

1997 v Dortmund – United drew a Borussia Dortmund side containing current Aston Villa boss Paul Lambert. The German outfit knocked United out 2-0 on aggregate, and went on to win the tournament when they beat holders Juventus 3-1 in the final.

1999 v Barcelona/Bayern, Inter, Juventus and Bayern again – Looking back it is quite remarkable to see how United navigated through both the group and the knock-out phases of the Champions League. Having had to face the best that Germany, Italy and Spain had to offer, no one can deny United were worthy of lifting the trophy that year. They progressed from the group of death containing Bayern and Barcelona, defeated Inter Milan in the quarter-finals and then miraculously Juventus in the semi’s. They then broke Bayer hearts in the final, netting twice in as many minutes late on to secure the trophy.

2000 v Real Madrid – United were stopped in their tracks of their European defence when they drew Real Madrid in the quarter-finals. Having done so well to return to Old Trafford with a 0-0 aggregate score line from the Bernabeu, they did not have enough to stop Raul and his gang from progressing. Madrid went on to be Champions.

2010 v Bayern – After dispatching AC Milan in the knock-out stages of the competition, United were rekindled with their German nemesis Bayern Munich. The reds returned to Old Trafford 2-1 down from the first leg, and got off to an explosive start when goals from Darron Gibson and Nani put them 3-0 ahead. This has United 4-2 ahead on aggregate, with the advantage of an away goal. But strikes from Olić and Robben soon crushed hopes of a third consecutive European final.

2013 v Real Madrid – Last season’s draw saw United face Real Madrid for the first time in a decade. It was also the first time fans got to see Cristiano Ronaldo return to Old Trafford since his departure from United in 2009. A positive 1-1 draw at the Bernabeu put Alex Ferguson’s men in charge of the tie, and it got even better when Sergio Ramos’ deflected own-goal increased United’s lead. But an exquisite strike from Luka Modric and then a Ronaldo tap in after Nani was controversially red-carded for a high-tackle, saw the nine-time champions progress.

United cannot escape the immense difficulty facing their quarter-final draw later today, but can look to the stars of 1999 to inspire what will need to be a miracle for Moyes and his men.

Do United have a chance of progressing beyond the quarter-finals in Europe?

Dan Connor

Dan is a sports journalism undergraduate from Barry, South Wales. He is a club journalist at West Bromwich Albion and a weekly writer for The Independent’s sport section. Previous work for BBC Sport, BBC Radio and Manchester United has seen Dan cover a range of sport such as rugby union, tennis and Formula One. His expertise lies in Welsh football, in particular with Cardiff and Swansea City.